Acrylate-ureadiacetoacetamide-diacetoacetamide copolymers

Abstract

Crosslinked random acrylate-ureadiacetaoacetamide-diacetoacetamide copolymers are disclosed. These copolymers are prepared by the reaction of at least one polyfunctional acrylate with at least one ureadiacetoacetamide and at least one diacetoacetamide in the presence of a catalyst capable of promoting the reaction between the polyfunctional acrylate, the ureadiacetoacetamide, and the diacetoacetamide. In a preferred embodiment, the copolymers are employed to produce wear layer compositions for surface coverings.

What is claimed is: 
     
       1. A cross-linked random acrylate-ureadiacetoacetamide-diacetoacetamide copolymer produced by the reaction of at least one polyfunctional acrylate with at least one ureadiacetoacetamide and at least one diacetoacetamide in the presence of a catalyst capable of promoting the reaction between the polyfunctional acrylate, the ureadiacetoacetamide, and the diacetoacetamide. 
     
     
       2. The cross-linked random copolymer of claim 1 in which said polyfunctional acrylate has the formula   R--O--C(O)--CH═CH.sub.2).sub.4     wherein R represents ##STR10##   
     
     
       3. The cross-linked random copolymer of claim 1 in which said polyfunctional acrylate has the formula   R.sup.1 --O--C(O)--CH═CH.sub.2).sub.3     wherein R 1  represents ##STR11## and R 3  represents hydrogen or (C 1  to C 3 ) alkyl.   
     
     
       4. The cross-linked random copolymer of claim 1 in which said polyfunctional acrylate has the formula   R.sup.2 --O--C(O)--CH═CH.sub.2).sub.2     wherein R 2  represents: a (C 1  to C 10 ) alkylene group, a (C 1  to C 4 ) alkyl substituted (C 1  to C 10 ) alkylene group, --C 2  H 4  O-- a  --C 2  H 4  --, ##STR12## --CH 2  CH 2  CH 2  CH 2  O-- c  CH 2  CH 2  CH 2  CH 2  --, a cycloalkylene group, a cycloalkane bearing two (C 1  to C 3 ) alkylene groups, ##STR13## a is an integer from 1 to 20; b is an integer from 1 to 10; and c is an integer from 1 to 5.   
     
     
       5. The cross-linked random copolymer of claim 1 in which said ureadiacetoacetamide has the formula   H.sub.3 C--C(O)--CH.sub.2 --C(O)--NH--R.sup.4 --NH--C(O)--HN--R.sup.5 --NH--C(O)--HN--R.sup.4 --NH--C(O)--CH.sub.2 --C(O)--CH.sub.3     wherein R 5  represents: 2,2,4-trimethylhexamethylene, 2,4,4-trimethylhexamethylene, mixtures of 2,2,4-trimethylhexamethylene and 2,4,4-trimethylhexamethylene, methylenebis(4-cyclohexylene), and 3-methylene-3,5,5-trimethylcyclohexylene; wherein each R 4  may be the same or different and separately represents: a (C 1  to C 10 ) alkylene group, a (C 1  to C 4 ) alkyl substituted (C 1  to C 10 ) alkylene group, --C 2  H 4  O-- d  --C 2  H 4  --, ##STR14## a cycloalkylene group, a cycloalkane bearing two (C 1  to C 3 ) alkylene groups, --H 6  C 3  O--C 2  H 4  O-- e  --C 2  H 4  ----OC 3  H 6  --, ##STR15## d is an integer from 1 to 6; and e is an integer from 1 to 4.   
     
     
       6. The cross-linked random copolymer of claim 1 in which said diacetoacetamide has the formula   R.sup.4 --NH--C(O)--CH.sub.2 --C(O)--CH.sub.3).sub.2     wherein R 4 , d, and e are as defined above.   
     
     
       7. The cross-linked random copolymer of claim 1 wherein from about 1 to about 2 moles of polyfunctional acrylate are employed for every 1 mole of total ureadiacetoacetamide and diacetoacetamide, wherein said 1 mole comprises ureadiacetoacetamide in an amount of from about 0.1 to about 0.9 mole. 
     
     
       8. The cross-linked random copolymer of claim 1 wherein from about 1.2 to about 1.4 moles of polyfunctional acrylate are employed for every 1 mole of total ureadiacetoacetamide and diacetoacetamide, wherein said 1 mole comprises ureadiacetoacetamide in an amount of from about 0.1 to about 0.9 mole. 
     
     
       9. A cross-linked acrylate-ureadiacetoacetamide copolymer produced by the reaction of at least one polyfunctional acrylate with at least one ureadiacetoacetamide in the presence of a catalyst capable of promoting the reaction between the polyfunctional acrylate and the ureadiacetoacetamide. 
     
     
       10. The cross-linked acrylate-ureadiacetoacetamide copolymer of claim 9 in which said polyfunctional acrylate has the formula   R(O--C(O)--CH═CH.sub.2).sub.4     wherein R represents ##STR16##   
     
     
       11. The cross-linked acrylate-ureadiacetoacetamide copolymer of claim 9 in which said polyfunctional acrylate has the formula   R.sup.1 --O--C(O)--CH═CH.sub.2).sub.3     wherein R 1  represents ##STR17## and R 3  represents hydrogen or (C 1  to C 3 ) alkyl.   
     
     
       12. The cross-linked acrylate-ureadiacetoacetamide copolymer of claim 9 in which said polyfunctional acrylate has the formula   R.sup.2 --O--C(O)--CH═CH.sub.2).sub.2     wherein R 2  represents: a (C 1  to C 10 ) alkylene group, a (C 1  to C 4 ) alkyl substituted (C 1  to C 10 ) alkylene group, --C 2  H 4  O-- a  --C 2  H 4  --, ##STR18## --CH 2  CH 2  CH 2  CH 2  O-- c  CH 2  CH 2  CH 2  CH 2  --, a cycloalkylene group, a cycloalkane bearing two (C 1  to C 3 ) alkylene groups, ##STR19## a is an integer from 1 to 20; b is an integer from 1 to 10; and c is an integer from 1 to 5.   
     
     
       13. The cross-linked acrylate-ureadiacetoacetamide copolymer of claim 9 in which said ureadiacetoacetamide has the formula   H.sub.3 C--C(O)--CH.sub.2 --C(O)--NH--R.sup.4 --NH--C(O)--HN--R.sup.5 --NH--C(O)--HN--R.sup.4 --NH--C(O)--CH.sub.2 --C(O)--CH.sub.3     wherein R 5  represents: 2,2,4-trimethylhexamethylene, 2,4,4-trimethylhexamethylene, mixtures of 2,2,4-trimethylhexamethylene and 2,4,4-trimethylhexamethylene, methylenebis(4-cyclohexylene), and 3-methylene-3,5,5-trimethylcyclohexylene; wherein each R 4  may be the same or different and separately represents: a (C 1  to C 10 ) alkylene group, a (C 1  to C 4 ) alkyl substituted (C 1  to C 10 ) alkylene group, --C 2  H 4  O-- d  --C 2  H 4  --, ##STR20## a cycloalkylene group, a cycloalkane bearing two (C 1  to C 3 ) alkylene groups, --H 6  C 3  O--C 2  H 4  O-- e  --C 2  H 4  ----OC 3  H 6  --, ##STR21## d is an integer from 1 to 6; and e is an integer from 1 to 4.   
     
     
       14. The cross-linked acrylate-ureadiacetoacetamide copolymer of claim 9 wherein said polyfunctional acrylate is reacted with the ureadiacetoacetamide in a mole ratio of from about 1 to about 2 moles of polyfunctional acrylate to about 1 mole of ureadiacetoacetamide. 
     
     
       15. The cross-linked acrylate-ureadiacetoacetamide copolymer of claim 9 wherein said polyfunctional acrylate is reacted with the ureadiacetoacetamide in a mole ratio of from about 1.2 to about 1.4 moles of polyfunctional acrylate to about 1 mole of ureadiacetoacetamide.